After five seasons, HBO's hit show Insecure [1] is coming to an end. We've gotten to watch Issa and Molly grow into more mature versions of themselves, and we've seen that, just like other 30-somethings, they had several relationships and flings along the way. Just like their characters, Issa Rae, Yvonne Orji, and the rest of the Insecure cast have blossomed professionally over the last five years, with Issa securing an eight-figure deal with WarnerMedia in 2021 and cast members like Amanda Seales and Natasha Rothwell going on to have successful TV careers [2].
The Insecure cast members have also grown a lot personally over the years. Throughout that time, some have found successful relationships of their own. Read on to see who's single and who's taken.
Who Is Issa Rae Dating?
Issa Rae has largely kept her private life out of the public eye. But in July 2021, Issa celebrated her marriage to businessman Louis Diame [3] with a gorgeous wedding in the South of France. She wore a stunning custom Vera Wang gown and was surrounded by friends and family for the ceremony.
Issa opened up about life as a newlywed [4] to Self in a September 2021 cover story. "I'm extremely happy," she said. Even though she prefers to keep her private life private, she knew that she had to share photos of her wedding on her Instagram (with a hilarious caption) [5] to break the news to the world. "I still try to be private about my personal life, but that was something that I knew was going to be shared, and I just wanted to share it on my own terms," she said. "There's something really nice to have a piece of me that no one knows about or no one can talk about except for the people that are part of my life."
Who Is Yvonne Orji Dating?
Yvonne Orji has acknowledged that she's very different from Molly, her character on Insecure. Unlike the 30-something lawyer, Yvonne is a virgin in real life. "I'm a virgin and I'm playing this girl on TV who's like sexually free [6]. And there are days that I would go home from set and I'd just be like, 'I want somebody to come over.' And it's like 'No, go to bed,'" she once said in an interview with Fusion [7].
Yvonne was previously in a relationship with sports commentator and The Bachelor [8]'s After the Last Rose host Emmanuel Acho. The two dated for a little over a year from 2018 to 2019. These days, Yvonne appears to be single and focusing on herself.
Who Is Jay Ellis Dating?
Jay Ellis largely kept his love life private throughout most of Insecure's run. But in a 2020 Essence cover story, Ellis reflected on fatherhood after welcoming his daughter, Nora Grace Ellis, with his longtime girlfriend, model and actress Nina Senicar, in 2019. "When you're pushed to the limits, whether it's personally ... with a baby, and you're up all night, or whether it's with work, you start to realise your limits aren't what you thought they were," he admitted. "I'm tired, but I can actually do it, and nothing has to suffer. I didn't want to not be there for my baby [9] ... I wanted all of that, and I wanted to make my episode the best it could possibly be."
Who Is Amanda Seales Dating?
After dropping hints for over a year, Amanda Seales spoke about her relationship in a May 2021 Instagram Live. She hasn't revealed his name or his identity, but she revealed that they met her freshman year of college at SUNY-Purchase [10].
"We were together for like a year and a half, and then he transferred," she said. "And then over the next 20 years, we were friends, and he lived his life, and I lived my life, and then we reconnected and voilà." When asked how exactly they reconnected, Seales said that she sent him a random text one night. "I hadn't talked to him in five years and by the next morning, we were back together."
Who Is Natasha Rothwell Dating?
Natasha Rothwell once jokingly tweeted that her boyfriend was Idris Elba, but the actress and screenwriter [11] appears to be single based on her social media profiles.
Who Is Kendrick Sampson Dating?
Kendrick Sampson hasn't revealed any details about who he's dated in the past, and judging by his social media, he appears to be single now. But over the years, unconfirmed rumours tied the Flash actor to stars like Naomi Campbell [12], Normani, and even Issa Rae herself.